9 Celebrity Odd Couples with a Big Age Difference

Defying logic and a nearly twenty-year age-difference, Amber Tamblyn and David Crossannounced their engagement yesterday. We knew they'd been dating because of what a strange pair they were — the snarky girl from Sisterhood of the Traveling Pants and Tobias from Arrested Development — but we sorta figured they'd broken up by now.

The fact that they're engaged puts these guys at the front of the list of couples that make you think “How did they even meet?” and “She's with him?” (And on some occasions, “He's with her?”) Adding to the novelty of the situation is the fact that many of these strange pairings have quite the age difference.